Your dreams are but a fickle, untenable part of your imagination, and the only way you seem able to realize or even comprehend them, is through the lens of another: that mysterious potential mentor. That distant connection you know could help your career if only you could get a meeting! Maybe you stumbled across this person on LinkedIn, maybe you caught them talking on a panel, or maybe they’re your best friend’s uncle who’s a fancy CEO that you have idolized for years. Wherever you found her, they’ve become a small obsession of yours, an almost fantastical creature, designed to prove that yes, your dreams could indeed come true. And now you’ve found yourself wondering, what would happen if I met this person? 

How do you write that first email to a potential mentor?

The solution is simple: find their contact details, and reach out. In your email, try “connecting offline” in the subject line. They will know you’re serious, and they’ll even be a little bit interested. You could potentially be the most exciting or unusual email they will receive that day. Who knows? What we do know is an over-the-top exclamatory subject line is not only going to come across gaudy, but will read more like a PR pitch that they’ll send to trash or spam. Let’s avoid that. Also when signing off, thank them for their time. Reserve “Best,” for your worst enemies and/or annoying bosses.

And for everything in between? The bulk, the body of the email that will make or break your chances to connect with your dream mentor? Trust me — it’s not as distant a dream as you think. Just follow these four pointers to get you on that coffee date — and build a mentor relationship that will take your career to the next level.

1. Flatter subtly, and with taste.

Millennials are prone to using the word “obsessed,” as if every other idolization in their vocabulary has suddenly and miraculously disappeared. Leave this out of your message. You’re not obsessed with their work. You really admire what they’ve done, you’ve been following their career, and if you’re really schmoozing, you might mention that they’ve been an inspiration to you (reserve this for someone whose ego you assume will enjoy it). Chances are, you’re not emailing the Dalai Lama. If you’re too over the top with praise, you run the risk of sounding uncouth. Deliver one line of praise and be done with it. After all, you may be worth something to them, too.

2. Summarize your accomplishments, briefly.

This is not a message to a recruiter or HR. Rather, this is a semi-formal, “I would love to meet you” email. When introducing yourself and your background, throw in something that will make them want to meet you, too. Ask yourself: “What about me will resonate with them?”

Ask yourself: “What about me will resonate with them?”

Did you take the same college course, or pave the same career path when you were starting out? Let it be brief and let it stand out, but do not let it be longer than the flattery mentioned above. Nobody is going to meet an egomaniac for fun.  Intentionally share your accomplishments, but don’t let it go on too long.

3. Leave the exclamation points at home.

You’re not texting a group or sending a DM; this is serious business. There shall be no emojis or exclamation points. You are not over-excited or hyper — you are calm, poised and all-business. Sure, if the meeting goes well you can come back later and spam that dancing senorita or aubergine all you want — but for now, you’re looking for conversation and guidance. This is a marathon, not a sprint, and chances are you’re emailing someone who’s important (she/he’s worthy of your time, right?), so act accordingly. Imagine yourself on the receiving end of this email in this position of power twenty years down the line. Would you be amused by platitudes?

4. Avoid the DMs. Try really, really hard to get an email.

An email is the nicest, most polite and most formal way to contact someone you want to meet for career advice and mentorship. A DM on Instagram or Twitter is very relaxed — and don’t get me started on Facebook. Although that is almost the entire premise of Linkedin, there’s a chance that they’re too big and important to check their hundreds of messages on that platform. This is why their inbox is the sweet spot, and where you’re going to have the best shot of being seen and taken seriously. This is not to say that reaching out via social would not prove fruitful. If you’re at a loss to find their email, and think you have a chance of setting a meet via these channels, go for it — as a last resort. Hot tip: if you happen to find an email belonging to a colleague of theirs (some people are more loose lipped with their contact info), try follow the formula of their email address to find the person you’re looking for. For example: You might just get lucky.

Be confident and articulate, but mostly, be passionate, and know what you seek from them before the meeting.

What you really have to remember about reaching out is that ultimately, they will be doing you a favor if they choose to meet — and not the other way around. There’s a reason you’ve found them among a sea of their peers as someone to look up to. Flatter, but don’t idolize: nobody likes a brown-noser. Be confident and articulate, but mostly, be passionate, and know what you seek from them before the meeting. Is it advice, their story, or their contacts? Ask, and you may receive.

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